Substituted oxazolidinone compounds and applications thereof

A compound and composition technology, applied in the field of medicine, can solve the problems of incurable infection and drug resistance, and achieve the effects of good pharmacokinetic parameter characteristics, changing dosage, and improving applicability

Active Publication Date: 2020-12-18
SHENZHEN TARGETRX INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing antibiotics are no longer effective against growing infections and drug resistance

Method used

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  • Substituted oxazolidinone compounds and applications thereof
  • Substituted oxazolidinone compounds and applications thereof
  • Substituted oxazolidinone compounds and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of (R)-3-(4-(2-(2-d3-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxy Methyloxazolidin-2-one phosphate (compound T-1)

[0040]

[0041] Concrete synthetic steps are as follows:

[0042]

[0043] Step 1 Synthesis of 2-(2-d3-methyltetrazol-5-yl)-5-bromopyridine (Compound 2).

[0044] 5-bromo-2-(2H-tetrazol-5-yl)pyridine (0.5g, 2.2mmol) and K 2 CO 3 (0.61g, 4.42mmol) was dissolved in 10mL DMF, and deuterated methyl iodide (0.42g, 2.88mmol) was slowly added dropwise under ice bath. After dropping, the mixture was stirred under ice bath for 1 hour, and TLC detected that the starting material disappeared. Add 40mL of water to the reaction solution, extract with ethyl acetate, wash the organic phase with 20mL of saturated brine, dry over anhydrous sodium sulfate, concentrate, and column chromatography to obtain the oily 2-(2-(methyl-d3)tetrazole -5-yl)-5-bromopyridine (compound 2) 0.27g, yield 52.5%. 1 H NMR (300MHz, CDCl 3 ) 8.8...

Embodiment 2

[0051] Example 2 Preparation of (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl-3,4,6-d3)-3-fluorobenzene Base) -5-hydroxymethyloxazolidin-2-one phosphate (compound T-2)

[0052]

[0053] Concrete synthetic steps are as follows:

[0054]

[0055] Step 1 Synthesis of 2-(2-methyltetrazol-5-yl)-5-bromopyridine (Compound 6).

[0056] 5-bromo-2-(2H-tetrazol-5-yl)pyridine (0.5g, 2.2mmol) and K 2 CO 3 (0.61g, 4.42mmol) was dissolved in 10mL of DMF, and iodomethane (0.41g, 2.88mmol) was slowly added dropwise under ice-cooling. After dropping, the mixture was stirred under ice bath for 1 hour, and TLC detected that the starting material disappeared. 40mL of water was added to the reaction solution, extracted with ethyl acetate, the organic phase was washed with 20mL of saturated brine, dried over anhydrous sodium sulfate, concentrated, and column chromatography gave 2-(2-methyltetrazol-5-yl )-5-bromopyridine 0.28g, yield 52.7%. 1 HNMR (300MHz, CDCl 3 ) 8.83 (d, J=2.3Hz,...

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Abstract

An oxazolidone compound represented by formula (I), or a crystalline form, pharmaceutically acceptable salt, prodrug, metabolite, stereoisomer, isotopic isomer, hydrate, or solvate thereof, and a pharmaceutical composition comprising the compound. The compound has demonstrated inhibitory activity against a broad spectrum of bacteria and low toxicity, and can be used to prepare an antibiotic.

Description

technical field [0001] The invention belongs to the field of medicine. Specifically, the present invention relates to deuterated oxazolidinone derivatives and uses thereof, more specifically, the involved oxazolidinone compounds can be used as antibiotics. Background technique [0002] Antibiotics are one of the most frequently used basic medicines in clinic. The non-standard use of antibiotics due to historical reasons has caused serious bacterial resistance to existing antibiotics. Multidrug-resistant (MDR) bacterial infections have become one of the major threats to global public health. Because of multidrug resistance, the combination of antibiotics is also increasing, and drug-drug interactions also increase the risk of adverse reactions. According to the 2013 National Adverse Drug Reaction Monitoring Annual Report released by the State Food and Drug Administration recently, the adverse reactions caused by antibiotics rank first in the adverse reaction / event reports....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6558A61K31/675A61P31/04A61P31/06
CPCA61K31/675C07F9/6558
Inventor 王义汉邢青峰
Owner SHENZHEN TARGETRX INC
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